Methods are known for preparing 4-(.alpha.-alkyl-.alpha.-cyanomethyl)-2,6-disubstituted phenols. For example, the preparation of 4-(.alpha.-alkyl-.alpha.-cyano-methyl)-2,6-disubstituted phenol by reacting .alpha.-alkyl-4-hydroxy-3,5-di-tertiary-butylbenzyl halides with sodium cyanide is reported by A. A. Volod'kin et al., Iz. Akad. Nauk. SSSR, Ser. Khim, 1966, 1031. Also, the preparation of 4-(.alpha.-alkyl-.alpha.-cyano-methyl)-2,6-disubstituted phenol by the electrochemical reduction of the corresponding 2,6-disubstituted methylene-quinones is reported by L. I. Kudinova, et al., Iz. Akad. Nauk. SSSR, Ser. Khim., 1978, 1313. U.S. Pat. No. 4,405,528 discloses a novel process for the synthesis of 4-(.alpha.-alkyl-.alpha.-cyanomethyl)-2,6-disubstituted phenols by reacting a 2,6-disubstituted phenol with a Friedel-Crafts addition agent in the presence of a Friedel-Crafts catalyst such as aluminum chloride to form the corresponding 4-(.alpha.-alkyl-.alpha.-oxomethyl)-2,6-disubstituted phenol, reducing the 4-(.alpha.-alkyl-.alpha.-oxomethyl)-2,6-disubstituted phenol to form the corresponding 4-(.alpha.-alkyl-.alpha.-hydroxy-methyl)-2,6-disubstituted phenol and thereafter reacting the 4-(.alpha.-alkyl-.alpha.-hydroxymethyl)-2,6-disubstituted phenol with an alkali metal or an alkaline earth metal cyanide to form the desired 4-(.alpha.-alkyl-.alpha.-cyano-methyl)-2,6-disubstituted phenol.
U.S. Pat. No. 4,483,800 discloses a method of preparing 4-(.alpha.-hydrocarbyl-.alpha.-cyano-methyl)-2,6-disubstituted phenols by reacting a 2,6-disubstituted phenol with an aldehyde and an alkali metal cyanide or an alkaline earth metal cyanide.
The synthesis of o- and p-hydroxy substituted phenylacetonitriles also is known and is reported in the literature. See for example, Journal of Organic Chemistry, Vol. 41, No. 14, 2502 (1976).
It has now been discovered that novel 4-(.alpha.,.alpha.-dihydrocarbyl-.alpha.-cyano-methyl)phenols can be prepared in a simple and straightforward manner. In this process, 4-(.alpha.,.alpha.-dihydrocarbyl-.alpha.-cyano-methyl)phenols are produced in a novel synthesis reaction and are deemed useful as antioxidants.